Phenethylamine → HCID 57695524, compound

HRID 2079858Notes

Reaction equation

HRID 2079858 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([C:23]2[CH:28]=[C:27]([CH:29]([CH3:31])[CH3:30])[CH:26]=[CH:25][C:24]=2[O:32][CH3:33])=[CH:11][C:10]=1[C:34](O)=[O:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH:49]1[CH:54]=[CH:53][C:52]([CH2:55][CH2:56][NH2:57])=[CH:51][CH:50]=1>CN(C=O)C.O>[CH2:56]([NH:57][C:34]([C:10]1[CH:11]=[C:12]([C:23]2[CH:28]=[C:27]([CH:29]([CH3:30])[CH3:31])[CH:26]=[CH:25][C:24]=2[O:32][CH3:33])[C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:35])[CH2:55][C:52]1[CH:53]=[CH:54][CH:49]=[CH:50][CH:51]=1

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 57695593HCID 57695593, compound

Product 1

HCID 57695524HCID 57695524, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

4,6-Bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-carboxylic acid (965 mg, 2 mmol) was dissolved in DMF (anhydrous, 10 ml), and CDI (324 mg, 2 mmol) was added and the resulting solution was stirred at r.t for 2 h. 2-Phenethylamine (267 mg, 2.2 mmol) solution in DMF (5 ml) was added and the resulting solution was stirred at r.t. until the reaction was complete. The reaction was diluted with water (50 ml), extracted with dichloromethane (50 ml×3), and the combined organics were washed thoroughly with water to remove DMF and dried over sodium sulfate. After filtration and concentration, the residue was purified by flash chromatography on silica gel to give 4,6-bis-benzyloxy-5′-isopropyl-2′-methoxy-biphenyl-3-carboxylic acid phenethyl-amide (1101 mg, 94%). M.p.: 138-140° C.; 400 MHz 1H NMR (CDCl3) δ: 8.17 (s, 1H), 7.87 (t, J=5.6 Hz, 1H), 7.40-7.36 (m, 3H), 7.32-7.11 (m, 14H), 6.87 (d, J=8.0 Hz, 1H), 6.54 (s, 1H), 5.03 (s, 2H), 5.00 (s, 2H), 3.72 (s, 3H), 3.64 (q, J=6.4 Hz, 2H), 2.92-2.81 (m, 1H), 2.75 (t, J=7.2 Hz, 2H), 1.23 (d, J=7.2 Hz, 6H); LCMS: 586 [M+H].

Workup

  1. stirringthe resulting solution was stirred at r.t. until the reaction
  2. extractionextracted with dichloromethane (50 ml×3)
  3. washthe combined organics were washed thoroughly with water
  4. customto remove DMF
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-1a944c50e88047fdbacb6a27a1c75056
Source dataset
uspto-grants-2011_04
Patent number
US07932279B2

Reaction notes

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